Even a navy blue dress ,sailor-inspired, should get some play in your winter wardrobe. I'm really not a fan of switching out my spring/summer and fall/winter clothes as I like to wear all of my stuff all year round. I don't usually wear this much short dresses but I have this one. I like the combination of a lighter dress and a heavy coat (when the weather allows me). And of course I added my newest hat and knee high faux suede boots (even though I' am quite short).
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Let me know what you think!